Synthetic studies towards d-modified paclitaxel analogues

A synthetic sequence has been developed for the preparation of 9,10-O-diacetyl-4-desmethylene-4β-(3-butenyl)-4α-hydroxy-5-O-mesyltaxicin I-1,2-carbonate 3, an intermediate in the attempted synthesis of cyclobutane paclitaxel analogue. A series of reactions of 3 has been investigated, including the p...

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Bibliographic Details
Published in:	Journal of the Serbian Chemical Society Vol. 77; no. 11; pp. 1529 - 1539
Main Authors:	Matović Radomir, Saičić Radomir N., Ferjančić Zorana
Format:	Journal Article
Language:	English
Published:	Serbian Chemical Society 01-01-2012
Subjects:	radical allylation silyl protecting groups taxanes antitumor agents taxoids
Online Access:	Get full text
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Summary:	A synthetic sequence has been developed for the preparation of 9,10-O-diacetyl-4-desmethylene-4β-(3-butenyl)-4α-hydroxy-5-O-mesyltaxicin I-1,2-carbonate 3, an intermediate in the attempted synthesis of cyclobutane paclitaxel analogue. A series of reactions of 3 has been investigated, including the protection of sterically hindered C-4α hydroxy group and oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to unexpected instability of the DMS protecting group under basic conditions. [Acknowledgments. Financial support of the Ministry of Education and Science of the Republic of Serbia is acknowledged (Project No. 172027)]
ISSN:	0352-5139
DOI:	10.2298/JSC120626094F